52189-53-4

Upstream product

• 65616-27-5 N-propyl-N-benzylhydroxylamine 
• 622-30-0 N-benzyl hydroxylalmine 
• 24423-93-6 (Z)-N-propylidene(phenyl)methanamine oxide 
• 107-10-8 propylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 62348-98-5 5-oxo-3t-phenyl-2-propyl-isoxazolidine-4r-carboxylic acid methyl ester 
• 71504-37-5 4,4-dimethyl-3-phenyl-2-propyl-isoxazolidin-5-one 

Relevant academic research and scientific papers

S -Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.

Direct oxidative synthesis of nitrones from aldehydes and primary anilines using graphite oxide and Oxone

One-pot condensation/oxidation of aldehydes and primary anilines into nitrones using graphite oxide (GO) and Oxone as the oxidant under very mild reaction conditions is described. The proposed method provides a direct oxidative synthesis of various nitrones in good to excellent yields under metal-free conditions in short reaction times.

Regioselective synthesis of nitrones by decarboxylative oxidation of N- alkyl-α-amino acids and application to the synthesis of 1-azabicyclic alkaloids

Tungstate-catalyzed oxidation of N-alkyl-2a-amino acids with 30% H2O2 solution under phase-transfer conditions gives nitrones regioselectively in good yields: Using this method, stereodivergent synthesis of (R)- and (S)-4- (t-butyldimethylsilyloxy)-1-pyrroline N-oxides ((R)-17a and (S)-17a) was achieved. In addition, (R)- and (S)-3-(t-butyldimethylsilyloxy)-1-pyrroline N-oxides ((R)-45 and (S)-45) were prepared by catalytic oxidation of the corresponding chiral pyrrolidines in a regioselective manner. These chiral cyclic nitrones, 17 and 45 are versatile intermediates for the synthesis of optically active nitrogen heterocycles, since stereoselective additions of carbon nucleophiles to these chiral nitrones can be readily performed. Typically, ZnI2-mediated addition of ketene t-butyldimethylsilyi methyl acetal (29a): to (R)-17a gave the' cis-adduct, methyl (2R,4R)-[1,4-bis(t- butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (cis-30). In contrast, the addition of lithium acetylides 34 to the nitrone (R)-17a gave the trans- adducts, (2S,4R)-2-(1-alkynyl)-4-(t-butyldimethylsilyloxy)-1- hydroxypyrrolidines trans-35. These adducts are useful intermediates for syntheses of the nitrogen heterocycles (3R,5R)-1-aza-3- hydroxybicyclo[3.3.0]octane (37) and (6R,8R)-1-aza-8- hydroxybicyclo[4.30]nonane (38), respectively. The ZnI2-mediated addition of ketene silyl acetal 29a to the nitrone (R)-45 gave methyl (2S, 3R)-[1,3- bis(t-butyldimethylsilyloxy)pyrrolidin-2-yl]acetate (trans-50a), which was used for asymmetric synthesis of the Geissman-Waiss lactone ((-)-49).

Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines

Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the α and α' carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the α proton is involved in the rate determining step as shown by primary kinetic isotope effect.

Tungstate-Catalyzed Decarboxylative Oxidation of N-Alkyl-α-amino Acids: An Efficient Method for Regioselective Synthesis of Nitrones

The tungstate-catalyzed oxidation of N-alkyl-α-amino acids with hydrogen peroxide under phase-transfer conditions gives the corresponding nitrones in satisfactory yield.